An Interview With Vanessa Ogle
Exhibit empathy — When we listen to people’s words and experiences, we allow ourselves to really understand that person. Being empathetic is an important way to see human beings as just that and also helps us to not otherize or judge. Empathy is a superpower of mine. I’m the kind of person who cries when they hear about people they don’t know, because I can feel the pain they and their loved ones must be feeling. To me, it is a universal connector as the human experience is something we can all relate to.
In a world where diversity is often acknowledged but not always celebrated, we are taking a step forward to highlight the importance of inclusivity in building strong, vibrant communities. This series aims to explore the various facets of diversity — be it racial, cultural, gender-based, or within the differently-abled community — and understand how embracing these differences strengthens our social fabric. As part of this series, we had the pleasure of interviewing Starr Sackstein.
Starr Sackstein is an accomplished educator, author, and advocate, dedicated to transforming education through innovative practices. With a background in secondary education, she has championed student-centered learning, assessment reform, and technology integration. As an author of several influential books, including “Hacking Assessment,” Starr empowers educators globally with practical strategies for creating learner-driven classrooms. Her insights, shared through speaking engagements, workshops, and online platforms, inspire educators to reimagine traditional teaching paradigms. Starr’s commitment to fostering critical thinking, growth, and equity underscores her role as a thought leader shaping the future of education.
Thank you so much for joining us in this interview series. Before we dive into our discussion about celebrating diversity, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
School was always an escape for me and learning, a salvation from my awkward early interpersonal relationships. Growing up in a privileged place, with parents who always wanted to give my brother and me more than they had, landed me in a population of people I had a hard time relating to. I was clearly different than my peers — not in appearance necessarily, but definitely in the way I thought. My teachers understood me better than my peers did and those formative relationships with adults made an important lasting impression. Although I didn’t think I would be a teacher, when I became one, the job was just right. Sometimes we fight for what we know is right, and since I was convinced I’d be a writer first, the idea of teaching didn’t appeal to me. I had worked for a literary agent while I was at NYU and I learned quickly that was not a job I wanted for more than a short time.
After working in desktop publishing and then in IT, I went back to graduate school to get my Master’s degree in Education. During that time, I also got my first teaching job while I was still learning. The idealism I approached my first few classes with shifted drastically once I made it to my own classroom and realized both the rigors and myths of teaching provided a counter-narrative. My first job was in a “high-needs” school in the inner city of NY. Although it wasn’t far from where I grew up geographically, it was a different universe from the one I was accustomed to. I learned quickly that I wasn’t as prepared to teach as I thought I was and I was so close in age to many of my students. Because I was new and had no idea what I was doing, obviously I was given the hardest classes — the ones that other teachers struggled with. Of course, I had nothing to compare it to, but I certainly questioned my choice to be a teacher a lot in those first few months, crying in corners and just trying to make it through the day. I wanted to be the kind of teacher they would remember for all of the right reasons, but first I had to let go of what I thought teaching was and embrace what it actually is. And once I stopped talking and started listening, I was able to connect better with my students.
Many challenges were working against me in this first job — my ignorance highest on the list. My compassion and ability to build relationships is what brought the kids to class every day, but my ability to get them involved and invested in their learning took time. I didn’t look like most of them — I was usually the only white person in the room. And I learned quickly I couldn’t make assumptions anymore (and didn’t want to), but had to be curious about these young humans with whom I was now linked significantly.
My first three years of teaching in this inner-city school made me the teacher I would become. My students taught me new things about their lives and experiences daily and I worked hard to support them in a way that worked for them — without trying to be anyone’s savior. I fear that those kids didn’t get the best version of me as a teacher because I was so green, but I know I gave them everything I had the capacity to at that time. Fortunately, social media has offered me a chance to be a voyeur in their lives and I’m touched that I made an impact on many of their lives as they had on mine.
Can you share an interesting or hopeful story where spending time with someone who did not look like you or who was different from you taught you something that has been useful to you?
As I boarded the plane to South Korea, I had really little idea what to expect. Just a month before I went to Dubai for the first time and aside from that, the farthest and most exotic place I had traveled was France after studying French for more than eight years in middle school through college.
Although anxiety existed, my excitement for this new adventure overcame it, and when I got off the plane at my final destination of Daegu (more than a whole day later with the time change), I eagerly looked around, taking in each new sight, seeking out my new friend with whom I’d corresponded for months now.
Fortunately, he spotted me first. Not too hard to do actually, as I have purple hair and I don’t look like the native people from that area.
“Starr Sackstein?” he asked, almost certain he was right.
“Yes, that’s me. How did you know it was me?” I asked.
“I just had a hunch.” He smiled warmly and offered to carry my bags, but I was fine as we walked to his car.
The weather in South Korea is a lot like it is in New York in October. Jason explained to me that the weather had just turned colder, and I shared that the same thing happened in New York. It was sunny out though, and the colors of autumn were all around us.
We eagerly chatted our way to breakfast in a place that he had never been to. I was nervous because my stomach doesn’t always respond well to new foods, but I didn’t want to seem ungrateful. The food was OK, and interacting with my Korean guide and friend was interesting. I asked him dozens of questions about the cultural norms. Trying not to seem so surprised by what I was learning; I took it all in.
One-on-one, it was easy to be with Jason. His English was very good, and he went out of his way to be a great host. It was at this time that he told me he wouldn’t be at the reception that night and that his colleague would pick me up and take me instead.
That first night after a long travel, I went to a lovely reception for the various important people attending the conference. I was the only American in the room and the only non-Korean speaker.
While I enjoyed dinner and the company of those around me, and several of the guests went out of their way to make me feel welcomed, I felt a little isolated. They all shared a culture, a language, and experiences as college professors that I couldn’t relate to.
While sitting at that table and then at various other times throughout the weekend, I couldn’t help but think about our English language learner students who are new to our country, some who don’t know the language or the cultural norms. This was the first time in my life that I felt like an outsider in this way. In my youth, and sometimes in my adult life, I’ve felt different, but not unable to communicate. If anything, my ability to communicate who I am and what I stand for has always been a strong characteristic of mine, so I can’t honestly say that being without words was easy.
Being in this position has made me acutely aware of how isolating not being able to understand a language is. The people I was with were extremely accommodating, so it wasn’t about that; it was about my frustration for not being able to communicate in the language of everyone around me who seemed to understand each other in a way I couldn’t.
As I returned home from this new experience, I was left with some questions that need pondering in our situations at home:
- How do we engage students who are new to our country?
- Even if we are polite and welcoming, what do we do to help them feel less isolated?
- In what ways can we help them integrate without diminishing the importance of where they come from?
- How can we be more mindful of how we speak around them?
- Is our normal side banter more isolating if we do it around students who struggle to understand what we mean?
- What can we do to combat the loneliness of these students and improve their time in school?
As educators, we must make school a safe place for all students. Children should know they can trust us and should never feel like it is OK to be isolated in any way.
The experience has profoundly impacted my views on any marginalized group at school. One of our basic human needs is to feel like we fit somewhere, and if we don’t feel safe in this way, learning can never happen.
You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Part of being a good educator and leader is being able to see people for who they are without judging them; as a matter of fact, you need to see into people’s hearts and see their strengths. I’m able to keep an open mind and stay curious about new people. I work hard at creating safe spaces where my team are open to sharing their truths and we can exchange ideas in a meaningful way. All of us as humans are limited by our own experiences and being around people who have had markedly different experiences helps us grow. Additionally, we can’t allow the opinions of others to color our feelings about those we work with; instead, we need to meet people and form our own opinions. This is so when meeting students who have already been defeated by a system or new members of a team who may have come from a challenging environment. The last important trait is the ability to assume positive intent. Resolving conflict in productive ways requires parties to believe that harm wasn’t intended. One story that comes to mind is from when I was a college student. Attending a county fair where my roommate was in the running for rodeo queen, and one of her 4H proteges asked me where my horns were when she found out I was Jewish. This is a misconception that she learned that I had an opportunity to address. I was quite happy to be the first Jewish person she met and was able to have a conversation with her about why what she was saying could be harmful. These kinds of one-on-one conversations have also been a highlight of how I’ve learned and developed some of my antiracist practices. Trusted friends who can honestly tell me when something I do can be hurtful or misconstrued. We don’t know what we don’t know and having someone safe point things out can be helpful. One other place that I was able to explore my own implicit bias was through Harvard’s online quizzes that help you identify areas you need to be mindful of.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal story that highlights the impact of diversity and inclusivity in your life or career?
As hard as it is to say, unfortunately, when inclusivity doesn’t exist, this can be a very triggering and traumatic experience. In one of the schools I worked in, I was explicitly told not to tell my students that I was Jewish. This was crazy to me because my last name sounds Jewish and I’m proud of my Judaism. I was perplexed by this declaration but later learned that there was a “whites only” country club next to the school and apparently, I wasn’t white enough. For the two years that I worked at this school when folks wished me a Merry Christmas, I just said Thank you instead of correcting them. The impact of denying a part of who I am to fit into the school community was an insidious mistrust and feeling of isolation which was compounded by the fact that I was a very different teacher than most of the folks I worked with. I never really fit in and although it isn’t ideal, I’ve spent a good portion of my life feeling like an outsider because I’m eccentric and don’t run with the crowd. I’m not afraid to be different. Because of these experiences, I’m acutely aware of what it looks like and feels like and so I work extra hard to make sure that people feel seen, accepted, and truly valued. The voices of the folks on my team, particularly those who are different from me deeply enrich our shared understanding. Being able to value the perspectives of others and see them through their eyes helps me grow as a person. It’s easy to make judgments and assumptions but these can be very damaging to a group dynamic. As a leader, I have to lead by example. When I make mistakes, I have to own it and ask for clarity. This is very humbling. We have to be careful with our words and expressions as we navigate differences so that no one feels alienated.
How do you approach and manage the challenges that arise when working towards creating more inclusive communities?
I need to be transparent and honest. When I see folks behaving in a way that is damaging to causing harm either intentionally or unintentionally, I have to say it aloud and make a point of addressing it before it has time to do further harm. These can be difficult conversations. The first time, it can be a private conversation using “I statements” to help the person understand the impact of what was said or done. A lot of folks don’t even realize that the words they choose or the looks they give can be triggering. So assume positive intent and share the impact. Additionally, as a group, we can try to repair harm using restorative practices where folks have the opportunity to confront each other in a safe environment. After the dialogue, I ask the folks to reflect and work through the feelings regardless of which side of the conversation they were on. We want to make sure that the same situation doesn’t occur again. If it happens again, we escalate the process for a different kind of intervention. The overall message is that no member of the team should feel unsafe — we can’t ignore microaggressions and pretend that they don’t have an impact on the team.
What innovative strategies or initiatives have you implemented or observed that effectively promote the importance of diversity and inclusivity?
Recently I became an online community leader and before they allowed us to do our jobs in the community, they expected us to take a DEI course that explained specific concepts and expectations. This course was flexible and timely and did a good job of mixing media to help important concepts of diversity and inclusivity come alive. As a person who presents as white, I’m extremely aware of my privilege and spend a good deal of time working on understanding different perspectives. This course helped me have deeper conversations with my son and other folks on my team. I do think it is important to make sure that our team has a shared understanding of expectations and more importantly why those expectations are in place. Additionally, as mentioned earlier, Harvard’s Implicit Bias quizzes can help individuals learn where they lean and once awareness is gained, individuals can work on developing strategies for ensuring they aren’t inadvertently behaving differently toward specific groups of people.
In your opinion, what are the key elements that make a community truly inclusive, and how can these be fostered on a larger scale?
Hallmarks of a truly inclusive environment include developing a real safe space. People should be able to speak their minds respectfully without fear of reprisal or repercussions. I’ve worked in several organizations that claim they care about what I think and feel only to lull me into a fake sense of security. I’ve opened up and shared some controversial opinions and ideas that are outside the status quo only to be yelled at publicly or shamed in front of my colleagues. This kind of behavior has the opposite effect. It got so bad that I had colleagues who would kick me under the table every time our leader would ask “What do you think of this?” as I often took the bait and regretted it afterward. I mentioned earlier that being curious is an important part of developing awareness of other perspectives and when I don’t agree with something that is being said, I have trained myself to listen first, ask clarifying questions, and then allow their responses to sit before I respond. A lot of being in an inclusive community is valuing other people’s ideas, cultures, and perspectives. We can’t do that unless we stop talking long enough to listen and understand without judgment. It has also been my experience that when folks are exposed to people they haven’t been exposed to before, we tend to otherize and sometimes even make assumptions that aren’t fair. This can be harmful to a community. It’s okay to not agree as long as it is done respectfully.
Based on your experience and research, can you please share “5 Ways We Can Build Inclusive Communities”?
1 . Be an active listener — Too often we make assumptions about people and their motives. So we need to slow down. Any opportunity we have to be an active listener to those around us increases our ability to be mindful and respectful of the group. While folks are talking, we can make eye contact and hold questions for later. It is also really important to not be thinking about what you want to say in response. This is a very defensive what to listen and can make situations where folks don’t feel heard — because they aren’t, frankly. If we expect our environments to change, we have to be a part of the change. This is something I struggled with as a younger person because I always wanted the opportunity to share my ideas. Because I hyperfocused on what I wanted to say, I missed a lot of what other people said which didn’t improve my overall understanding of the person. It also makes it harder for me to connect and build relationships.
2 . Be curious — When something seems off, rather than make assumptions or fill in the narrative with your own thoughts, stay curious. Respectfully ask questions to gain clarity and assume positive intent. When we approach situations by giving people the benefit of the doubt, we are less likely to put them on the offensive. One time that I struggled with this was as a new leader. I was responsible for observing and providing feedback to teachers on my team. Once I observed a teacher, and when she came in for post-observation, things became confrontational very quickly. It escalated quickly because of some assumptions I made and that she made as well. It was an important lesson. From that experience, I started scripting my observations and sharing the notes ahead of time with some wonderings, so that the teachers had time to think about my questions before talking to them about it. It also offered opportunities for them to provide evidence. This curiosity allowed folks to be less on guard and more open to suggestions. It also created a more collegial environment.
3 . Exhibit empathy — When we listen to people’s words and experiences, we allow ourselves to really understand that person. Being empathetic is an important way to see human beings as just that and also helps us to not otherize or judge. Empathy is a superpower of mine. I’m the kind of person who cries when they hear about people they don’t know, because I can feel the pain they and their loved ones must be feeling. To me, it is a universal connector as the human experience is something we can all relate to.
4 . Stay open to different perspectives — Taking the perspectives of others helps to empathize to deeply understand other people’s experiences. As a new leader, when we are first meeting our teams and building relationships, we must take the time to put ourselves in each other’s shoes to understand what they may be going through. Having this level of understanding with help empathy. Many times while I worked in the inner city, my colleagues would say things about my students and I worked hard to never allow someone else’s experience of a child color my view of them. Because I didn’t immediately make assumptions and I got to know each child and their perspectives, I was able to connect with the kids in a very authentic way, so I never had the same challenges my colleagues had.
5 . Celebrate and highlight diversity — Ask your team members how they like to be celebrated. Some folks don’t like public recognition and others thrive on it. Once you know your team and their preferences, highlight and celebrate the diversity and how it helps us be a stronger unit. You can do this in a newsletter, as a meeting, or right after you catch someone being awesome. We want to spread inclusive behavior and we can do that by example, we amplify our efforts to create an environment where all team members feel they belong and that their dignity is being honored.
How do you measure the impact and success of diversity and inclusion efforts, and what changes have you seen as a result of these initiatives?
The truest measure of impact and success on diversity is that folks feel represented and heard. All members of the community have opportunities to weigh in on important issues and their voices are a part of the deliberation. If policies and procedures aren’t effective, there are collective efforts to revise them as needed to ensure they are growing with the organization. There should be ongoing conversations to ensure that folks have the professional opportunities to learn and grow more personally. Infinity groups can be one way to create a safe space that allows like groups to share their experiences and then help unearth possible behaviors that need to be addressed in separate groups before coming back to the whole together. Additionally, individuals can monitor their own behaviors as they are aware of professional language that is supportive of the cause and make efforts to repair harm when missteps happen (and they will happen). We need to raise awareness of different perspectives and then ensure that that awareness translates into action.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
As an educator, I’d be remiss if I didn’t mention true education reform around assessment and grading. We start in this world building our identity in education environments and too many of them rank and judge learning in a subjective, meaningless way that harms the dignity of many young people. Real assessment and grading reform would honor the strengths that each learner brings to the table and take an asset-based approach to building expertise. If we can do this, we help build the confidence of youngsters and encourage them to share their voices, because they matter. I work with teams to build this awareness and practice. I have written many books on the topic.
How can our readers further follow you online?
I’m easy to find online. I have a website mssackstein.com and my company website masteryportfolio.com. I’m also heavily involved on LinkedIn under Starr Sackstein and Mastery Portfolio. They can find my collected written work on Amazon here: https://amzn.to/48aXfls
Other places:
X — @MsSackstein and @Masteryforall
Insta — @Starr53177
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
About The Interviewer: Vanessa Ogle is an entrepreneur, inventor, writer, and singer/songwriter. She is best known as the founder of Enseo which she and her team grew into one of the largest out-of-home media and connected networks in the world, serving more than 100,000,000 people annually. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion resulted in amazing partnerships and customer relationships. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Dish Networks to bring innovative solutions to the hospitality industry. Enseo has also held an exclusive contract to provide movies to the entire U.S. armed forces for almost 15 years. Vanessa and her team’s relentless innovation resulted in120+ U.S. Patents. Her favorite product is the MadeSafe solution for hotel workers as well as students and children in their K-12 classrooms. Accolades include: #15 on FAST 100, 50 Fastest Growing Women-Owned 2018–2020, Entrepreneur 360 Best Companies 2018–2020, not to mention the Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year. Vanessa now spends her time enjoying her children, sharing stories to inspire and give hope through articles and speaking engagements. entrepreneurs-to-be with her articles including her LinkedIN newsletter Unplugged. In her spare time she writes music with her husband Paul as the band HigherHill, teaches surfing clinics, and trains dogs.
Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack.
Celebrating Diversity: Starr Sackstein Of Mastery Portfolio On How To Build Inclusive Communities was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.